Pyridine → 2-Fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrile

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Reaction Steps

A mixture of 2-fluoromethyl-2-phthalimido-5-hydroxypentanenitrile (42.8 g), dry pyridine (170 ml), and dry dichloromethane (350 ml) is stirred and cooled with ice/salt mixture. Freshly distilled methanesulfonylchloride (15.7 g) in dichloromethane (200 ml) is slowly added, and stirring is continued at room temperature overnight. The mixture is then poured onto ice/2N HCl, and the organic phase is extracted subsequently with 1N HCl, water, 10 % sodium bicarbonate, and water (3×). Drying (MgSO4), treatment with charcoal (room temperature), and evaporation gives 2-fluoromethyl-2-phthalimido-5-methanesulfonyloxypentanenitrile as a brown oil (42 g).

Provenance & Evidence